Ni(II) Bis(oxazoline)-Catalyzed Enantioselective Syn Aldol Reactions of N-Propionylthiazolidinethiones in the Presence of Silyl Triflates

Ni(II) Bis(oxazoline)-Catalyzed Enantioselective Syn Aldol Reactions of N-Propionylthiazolidinethiones in the Presence of Silyl Triflates

An enantioselective aldol reaction of N-propionylthiazolidinethione and representative aldehydes is disclosed. The reaction is catalyzed by [Ni(S,S)-t-BuBox](Otf)2. Enolization is effected by 2,6-lutidine, and TMSOTf facilitates catalyst turnover. Syn diastereoselectivities range from 88:12 to 97:3,...

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Veröffentlicht in:Journal of the American Chemical Society 2003-07, Vol.125 (29), p.8706-8707
Hauptverfasser: Evans, David A, Downey, C. Wade, Hubbs, Jed L
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemical synthesis
Chemical reactivity
Chemistry
Exact sciences and technology
Ketones - chemical synthesis
Ketones - chemistry
Models, Molecular
Nickel - chemistry
Organic chemistry
Organometallic Compounds - chemistry
Oxazoles - chemistry
Reactivity and mechanisms
Silanes - chemistry
Stereoisomerism
Thiazoles - chemistry
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Beschreibung
Zusammenfassung:An enantioselective aldol reaction of N-propionylthiazolidinethione and representative aldehydes is disclosed. The reaction is catalyzed by [Ni(S,S)-t-BuBox](Otf)2. Enolization is effected by 2,6-lutidine, and TMSOTf facilitates catalyst turnover. Syn diastereoselectivities range from 88:12 to 97:3, and enantioselectivities are 90% or greater. Both aromatic and enolizable aliphatic aldehydes are included within the scope of this aldol addition process.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja035509j